Windy City
by jackphd
Summary: Elena, after losing her family in a tragic accident, is sent to Chicago to live with her aunts Liz and Jenna and her cousin Caroline. Damon, a junior at the University of Chicago, is struggling to find meaning in his still developing life. Though their differences are very apparent, the two may have more in common than they think. AU/AH Delena
1. Chapter 1

**Windy City:** A Story of Love in Chi-town

This is my first fic. Please rate and review, I'd really appreciate any criticism. Thanks!

P. S. First chapter is kind of short. I promise the next one will be longer and will have much more DE.

* * *

 **Elena**

As she weaved her way through O'Hare Airport, dragging her modest suitcase behind her and feeling her backpack begin to slip off her shoulder, Elena Gilbert could feel herself starting to cry.

It was something she had been doing quite frequently over the past few weeks. Since the accident, it seemed Elena could be brought to tears by even the slightest hint or reminder of her family. She had always been very emotional, which didn't exactly help in the grieving process. The droves of distant acquaintances and forgotten relatives back in Virginia asking her how she was or making the dreaded empty promise of "If you need anything, just let me know" didn't either. Everything she saw, everyone she talked to, everywhere she looked, there would be something that brought it all back.

But as Elena felt the salty tears begin to well up in her eyes after passing one of the shitty little airport bookstores in which her brother Jeremy always insisted browsing whenever they flew, she was able to stop herself for the first time. Coming to Chicago was supposed to be a fresh start, a new beginning, where she would no longer be the sad girl who lost her family. And that meant no more tears. Well, maybe some tears. But definitely no more the pathetic kind she had been shedding.

As she thought more about where she was, Elena even smiled to herself a little once her eyes dried. The promise of living in a big city was exciting. She looked forward to meeting new people and seeing new things, even if she would have to do it without her parents and her brother. Since Elena was very young, she'd always dreamed of traveling, but despite the occasional trip to see a family friend or grandparent she hadn't done much in the way-

"Welcome to Chicago, Elena!"

Elena's head snapped to the left of the atrium, where her Aunt Jenna, Aunt Liz, and her cousin Caroline stood with a garishly colorful sign that read _Welcome Elena_ , complete with marker-drawn hearts and craft store ribbon. The small smile that had begun to creep across Elena's face transformed into a full-on grin as Caroline sprinted toward her and enveloped her in a bone-crushing hug.

"Good to see you," Elena greeted, her voice muffled against the immense volume of blonde curls surrounding her head.

"Oh my god oh my god I'm so glad you're here! I've been dying to meet you!" Caroline squealed in response.

"So you must be Caroline?" Elena questioned. She had never actually met her cousin; Jenna and Liz hadn't been together for very long. Elena's parents had been trying to organize a visit prior to the accident.

"Oh! I'm so sorry, where are my manners? I'm Caroline, your cousin." She stuck out her hand, which Elena had only just grasped before she was whisked away at light speed. "Come on!"

Caroline dragged Elena back over to where her aunts were still standing with the impressively constructed welcome sign. "Bet you can't wait to meet these two carpet munchers!"

Jenna rolled her eyes while Liz swatted Caroline's shoulder playfully. Elena just looked at them, confused as to what they were talking about. Caroline laughed and said "Oh, you know," bringing up her hand to her mouth and miming cunnilingus with two fingers.

Elena immediately blushed and looked at the ground. To say that she had never heard such blatant language was an understatement; people in the wealthy small town of Mystic Falls would never use profanity so openly.

Caroline laughed again and draped her arm around Elena's shoulders. "Alright, sorry. Bet you can't wait to meet these two women in a healthy homosexual relationship!"

Liz took on a wry smile. "Much better Caroline. Elena, I apologize for my daughter's lack of modesty. I'm Liz Forbes, but you can call me Aunt Liz, or just Liz if you prefer. We are very happy that you'll be staying with us."

After the two exchanged a bemused handshake, Jenna pulled Elena into a hug. "It's so good to see you Elena," she whispered. As she pulled away, Elena was extremely grateful that she didn't mention her parents. She had always loved her mother's younger sister, and this gesture only made her view Jenna in a more positive light.

"Alright moms!" Caroline exclaimed, placing her hands on her hips and flipping her hair like a pop star. "Should we show Elena the Lez Pad?"

Jenna, after Liz' mutters of "Really, Caroline? Really?", explained to Elena that they would take a cab back to the three bedroom apartment in which they all lived. As the four walked toward the airport's exit, Caroline jabbered on and on about how she would give Elena the famous "Caroline tour" of Chicago's best nightclubs and restaurants. Elena smiled at Caroline's relentless positivity, and as she stepped outside and saw the majestic Chicago skyline for the first time, she was hopeful.

 **Damon**

"Honestly, Damon, you have nothing to worry about. You've read the textbook about a hundred times, you've highlighted and re-highlighted your notes – which I didn't even know was possible, by the way – and you've attended pretty much every study group on campus. You're going to kick this exam's ass."

"I don't know Rick. Sociology is the first class I've really struggled with. I just can't seem to get any of it. I know I've prepared as much as I can, but I'm still-"

"Look, man. If your idea of struggling is going into the final with an actual passing grade in the class, I've had a hell of a lot more struggles than you."

Damon grinned and shrugged. "I'm a perfectionist, what can I say?"

The two men were sitting at the coffee table in their campus apartment, drinking leftover cheap beer from a long-ago rager amidst scattered papers and books. As a third-year student at the University of Chicago, Damon needed to get at least a B in his sociology course to maintain the scholarship that allowed him to go to school. No B meant no scholarship, no scholarship meant no school, and no school meant no future. That was not an option.

If only he could get his damn mind to focus.

As he checked his phone for the umpteenth time that night, Damon received a loud sigh from his roommate, who got up and walked to the kitchen, presumably to grab some more beer.

"I really don't think she's going to text back, man," Rick said, scowling at the lack of quality liquor in the refrigerator.

"You're probably right," Damon said glumly, throwing his phone at his feet and sinking back in his chair.

Rick walked back over and patted Damon on the shoulder.

"I know it's hard. You two were together for a while. But she's transferring halfway across the country next year. It had to happen to eventually."

Damon took a swig of his beer and ran his fingers through his coal-black hair. "To be honest, we really weren't what we used to be toward the end. I just didn't feel the same way anymore. But I really wish it didn't go down so badly."

Rick smiled sympathetically. "Tell you what. Tomorrow night after your exam, we're gonna go out on the town. Maybe get some pizza, maybe get hammered. But we are definitely not going to mention the name Katherine a single time."

"That sounds great Rick," Damon said, grateful for his best friend's support. "In that case, I should hit the hay."

"Yeah, I probably should too," Rick agreed, picking up the discarded bottles and throwing them in the bin by the door.

Damon raised his eyebrows. "So that means I'll actually get some sleep tonight, and not have to cover my ears with my pillow to avoid hearing Isobel's incredibly high pitched moans?"

Rick grinned. "Hey man, I'm not going to apologize for my talents."

The two said goodnight, and Damon climbed into bed after a pathetic attempt at cleaning up his study materials. As he stared at the ceiling in the darkness, the guilt and sadness he felt over his breakup with Katherine seemed to dissipate as he considered the impending summer break, and beyond that, his future. Finally free of the relationship that had consumed his life in an extremely negative way, Damon smiled, and for the first time in a while, he was hopeful.


	2. Chapter 2

**Chapter 2**

Hope you guys enjoy! Again, please review. I'd greatly appreciate any suggestions or criticism.

* * *

 **Elena**

After experiencing the apparently famous "Caroline tour" of the most important locations of Chicago's nightlife, catching up with her aunt Jenna, and generally getting to know the women she would be living with for the foreseeable future over the course of an unexpectedly long cab ride, Elena was more than ready to get a good night's sleep. She was tremendously grateful that the school year was over; the three months of summer break would be much needed to adjust to a completely new place before tackling something as overwhelming as attending a new school for her senior year of high school. As soon as the cab dropped the four off at the apartment building, Elena started to follow Liz and Jenna up to the door. Just as she lifted her luggage to carry it up the stone stairwell, she heard Caroline clear her throat behind her.

"Actually, Elena, I was thinking we could hit the town. It's still pretty early, and I could show you some of the best clubs up close and personal."

"Caroline, I've been in and out of planes all day and I'm really tired. I think I'm just going to go to bed," Elena responded sheepishly, shifting her feet back and forth out of guilt at Caroline's obvious disappointment.

"Oh. Yeah, that's probably a good idea," Caroline reassured, replacing her crestfallen expression with a supportive smile.

"I really appreciate the gesture, but honestly I wouldn't be much fun in this state anyway."

"No problem! But I insist that we go out tomorrow night. It's Friday, so everyone will be out. I can introduce you to my friends! They'll love you."

"Well, I-" Elena hesitated. She instinctively felt herself begin to reject the offer, but then remembered her personal promise she had made in the airport. _A new beginning. A fresh start._ The old, emotional, grieving Elena would have made up an excuse to get out of going, but the new Elena was going to hit the town and meet new people. "I would love to."

"Great! I can't wait."

Elena smiled and turned to walk up the stairs once more.

"Oh! Elena, one more thing."

Elena turned around again.

"I know you're going through a rough time. I'm only making these offers to try to get your mind off of whatever's getting you down. I'm sorry if I seem pushy," Caroline confessed.

Elena, surprised at this sudden lucidity from the bubbly and blunt girl she had been getting to know over the past few hours, nodded. "It's no problem, Caroline. I really appreciate it.

As Elena walked up the stairs (for real this time) she smiled to herself at the amount of kindness she was already being shown less than day after arriving in Chicago. And she seemed to have made a friend in Caroline; the blonde had originally seemed to be everything Elena wasn't, but she could see that they may have a lot more in common than she thought.

* * *

Elena followed Caroline up to the doors of a fancy looking club that the blonde had referred to as "The Mid". To say that Elena was nervous would be quite the understatement; the initial excitement of experiencing Chicago's nightlife and meeting Caroline's friends had given way to anxiety and apprehension. What if no one liked her? What if she was too boring? What if they knew about her family and spent the entire night trying to console her? It was almost too much to handle.

Caroline, seeming to sense Elena's nerves, grasped her hand comfortingly and said, "Elena, don't be scared. I know it's overwhelming, but we'll have fun. I promise."

Elena nodded, astounded by Caroline's ability to read her so well. She wasn't convinced, however, despite Caroline's confident tone. The nagging insecure thoughts in the back of her brain were still annoyingly present. Elena did her best to ignore them.

As the two girls drew closer to the entrance, Elena had a sudden realization. "Wait, Caroline! This is a club! They serve alcohol in there. How are we supposed to get in?"

Caroline smiled at her sympathetically, handing her a plastic card. "Oh honey, you have so much to learn."

Elena looked at the card, gasping when she saw her own face staring back at her. It read: _Elena Gilbert. Born June 22nd, 1994_. "Caroline, you got me a fake ID?" she exclaimed incredulously.

"Of course I did, Elena. How are we supposed to have any fun if we can't drink?" Caroline laughed. "I had it made right before you got here. Used your Facebook profile picture and everything. It's the best fake you can buy around here."

"I'm not so sure about this, Caroline…" Elena responded with uncertainty. She had had her fair share of alcohol; house parties in Mystic Falls were known to get pretty out of control. But this seemed different, more dangerous.

"Oh, it'll be fine. Just flash some cleavage at the bouncer and he'll barely even glance at it. Watch and learn."

Caroline walked up to the bulky man standing in front of the club entrance. "Hi! Me and my friend here are here to meet some people. Do you think you could make room for us?" She not-so-subtlety adjusted her low-cut sequined top so that it hung even lower.

The bouncer looked at her and gruffly demanded to see their IDs. As Caroline had said, he took a quick look at them before nodding. "You can go ahead on in."

Elena and Caroline shared a smile and walked inside, ignoring the groans and protests of the disgruntled members of the line that had formed in front of the club.

As the girls entered, the muffled thumping bass that Elena had heard outside grew steadily louder. Brightly colored lights began to enter her vision, and she took a deep breath so as not to be too overwhelmed. It wasn't long, however, before Caroline spotted one of her friends.

"Stefan, hey! How are you?" the blonde shouted over the loud music.

Elena looked up to see a stunningly attractive boy carrying an astounding quantity of drinks. He began to walk over, smiling at the sight of Caroline. Elena took a deep breath, scolding herself for being so nervous.

"Hey, Care. How's my favorite bombshell?" Stefan greeted. He hugged Caroline and gave her a gratuitous kiss on the cheek. His gaze fell on Elena. "Wow. You must be Elena. You are insanely gorgeous."

Stefan placed a similarly excessive kiss on Elena's cheek, which felt to her like it was about to burn off.

"Oh, Elena, don't be too flattered," Caroline said humorously. "He's queer as a three dollar bill."

"But don't you wish I wasn't, Miss Slutty McSlut Pants," Stefan retorted, laughing loudly. "We both know I'm exactly your type."

"Please, Stefan. You couldn't be any farther from my type. I prefer men who use less than an entire bottle of hair gel every single day."

Stefan puts his hands up to his carefully styled 'do in mock offense. "Don't rag on the hero hair, baby."

"Why don't you take us over to your table? I can't wait for Elena to meet everyone," Caroline asked.

"Sure thing." Stefan led them through the crowd of writhing bodies, still carrying the precariously constructed tower of drinks in his hands. They stopped at a table where a blonde-haired boy and a dark-haired Asian girl were in the midst of what looked like an intense debate. A shockingly beautiful brunette was sitting at the other end of the table, her face buried in her phone. They all looked up as Stefan, Caroline, and Elena drew near.

"Guys, this is my cousin Elena. She just moved here from Virginia. Elena, that blonde meathead is Matt, Stefan's boyfriend. And the one he's talking to is Anna." Matt and Anna both shook Elena's hand, seeming much more reserved than Stefan and Caroline, who had seemed more comfortable with overtly physical greetings.

"It's great to meet you guys. I'm really excited to live in Chicago," Elena said timidly, shifting her feet back and forth. She wasn't exactly used to being the center of attention.

"Well, I'm glad you're here at least. I'm fucking sick of Matthew over here," Anna spat out playfully. "Who in their right mind thinks that Aliens is a better film than Alien?"

"Jesus Anna, it's not my fault you can't tell a good movie from a bad one. I don't think it's so ridiculous that I'd rather see decked out space marines take down xenomorphs instead of Sigourney Weaver in her underwear," Matt shot back, completely unembarrassed by the shameless nerdiness of the conversation.

"Guys, would you stop talking about movies for one second? I'm trying to make Elena actually feel welcome," Caroline said in an exasperated voice.

"Agreed. Why don't we talk about something Elena wants to talk about? I was hoping by the time I got back with the drinks the Alien talk would be over," Stefan said, sitting down on Matt's lap.

"That's Aliens, Stefan," Matt corrected, flicking Stefan's nose while Anna rolled her eyes.

Elena cleared her throat. "Well, I actually like movies a lot." She was surprised at her own boldness.

"Yeah! I like her already!" Matt exclaimed, raising his glass toward Elena, who smiled bashfully.

Anna returned with a snarky comeback, sparking a conversation between her, Matt, and Stefan. Elena, noticing that the girl at the end of the table had not participated in the conversation, turned to Caroline and asked, "Who's that?"

"Oh, that Stefan's older sister. She's usually too cool to be seen anywhere near us, so I'm not sure what the deal is tonight."

"She's beautiful."

"Yep, and she knows it too. I've never met someone as full of themselves as Katherine."

 **Damon**

As he stepped out of the sociology classroom, Damon felt like the weight of the world had been lifted off his shoulders.

The liberated feeling he had experienced after his breakup with Katherine was only improved by his performance on the exam, which he was pretty sure he had aced. He was done with school for the year, a free man, with nothing else to do for the rest of the week but relax and get extremely drunk. Everything was looking up Damon.

His phone vibrated, receiving a text from Rick that read: _Half off drinks at The Mid tonight. 9?_ Damon grinned from ear to ear, excited for an evening of antics with his friend. He replied quickly: _Fuck yes._

* * *

"So, do you see anyone worthy of the great Damon Salvatore?" Rick asked. Damon could barely hear him, a combined result of the pounding dance music and Rick's slurred speech.

"Of course not, Rick. No one is worthy of this," Damon responded, pompously gesturing to his physique. Rick rolled his eyes and took another swig of bourbon.

"Does that mean you're over Katherine?"

"I think so. But at the same time I don't feel up to any one-night stands. It wouldn't feel right."

"Yeah, I hear you. Anyways, I gotta take a leak. Let me know if you see anyone that would be 'worthy' of yours truly." Rick set his drink down and stumbled off to the bathroom. Damon rolled his eyes; he knew Rick was too much of a pussy to ever be unfaithful to Isobel. Not that that was the only reason; Rick was a great guy, the best he knew. He'd never do something so shitty to the girl he loved.

Damon leaned back against the bar, swirling his drink in his hand. He glanced around the room, taking in the ridiculously gratuitous dancing that was going on all over the dance floor. Even if he was up to it, there was no one here that he would even consider talking to, all jokes aside-

Damon's thoughts ceased abruptly as his gaze swept across to a table at the edge of the room. There, sitting alone with a still full glass in her hand, was the most beautiful girl he had ever seen.

Damon Salvatore was not one to exaggerate. But just looking at this girl made his heart beat harder than it ever had before. He slowly took in her long, luscious brown hair, her big brown eyes, her perfectly shaped curves, feeling as though he could barely breathe.

It was unclear whether it was the alcohol, or the release of pressure he had felt all day, or simply his body making a decision before his brain could, but Damon felt himself walking across the room. Despite saying that he wouldn't chase another woman so soon after Katherine, there was something about this girl that reduced those thoughts to nothing.

He soon reached her table, feeling more and more nervous. Damon had started dating Katherine at the end of his freshman year, and before that he had never had any problem with talking to women. They were always immediately sucked in by his raven black hair, toned body, and icy blue eyes, so much so that not much talking had to be done at all. But this was something completely different. He felt like he was in high school all over again.

Trying his best to push away the anxiety he felt, Damon sat in one of the chairs across from her and cleared his throat. The girl didn't look up, instead keeping her attention focused on her still-full drink. He cleared it again. This time she brought her eyes up to meet his, looking extremely surprised to see someone there.

"What's a beautiful girl like you doing sitting all alone?" he asked with a smile.

She blushed bright red and looked back down, again mesmerized by her drink. "All my friends are over there dancing," she answered timidly, tucking a lock of her hair behind her ear.

 _She is so beautiful_ , Damon thought to himself. "And why aren't you?"

"I don't know. I'm just not in the mood I guess," she said, looking even more embarrassed.

Damon laughed. "Hey, you don't need to justify yourself to me. I've never been much of the dancing type either."

She giggled, looking up briefly to gaze into his eyes before returning to her drink.

"I'm Damon," he said, stretching his hand across the table. "And you are?"

"Elena," she introduced, taking his hand. It was so soft and warm, he could have held it forever.

"Elena. What a pretty name," Damon complimented, reluctantly withdrawing his hand. Elena blushed furiously again. _Wow, this girl must not get too many compliments_ , he mused. _That's just unacceptable._ "What brings you here tonight?"

"I just moved here from Virginia to live with my cousin. She wanted to take me out to meet her friends," Elena said.

"Ah. So what do you think of Chicago so far, Elena?" Damon inquired, repeating her name. He loved the way it sounded coming out of his mouth.

"I love it," she admitted. "It's a bit…"

"Overwhelming?" Damon finished. She nodded. "I know what you mean. I grew up in a small town too, so the city life was a bit of a shock. It's almost as if…"

He trailed off. Damon felt a lump forming in his throat as he looked behind Elena, where Katherine was in the midst of a heated makeout session with some guy. He felt his hands clench into fists.

"Damon? What's wrong?" Elena asked worriedly.

"It was really nice to meet you Elena, but I have to go." Damon stood up quickly, rage clouding his vision. He stormed away. _I just need some air to clear my head_ , he thought, heading toward the exit. Leaving the most beautiful girl he had ever seen to sit at a table all by herself.

* * *

 **Hope you guys don't hate me for the ending! Don't worry, I'm sure Damon and Elena will find their way to each other eventually.**


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